Water → Ethyl 5-fluorobenzo[b]thiophene-2-carboxylate

HRID 1479912Notes

Reaction equation

HRID 1479912 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=O.C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:18][SH:19].O>CN(C=O)C>[F:10][C:7]1[CH:8]=[CH:9][C:2]2[S:19][C:18]([C:17]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][C:3]=2[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 1376632,5-Difluorobenzaldehyde

Product 1

HCID 23261724Ethyl 5-fluorobenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2,5-difluorobenzaldehyde (217.28 μL, 2 mmol) and potassium carbonate (595.53 mg, 2.5 mmol) in DMF (3 mL) was added ethyl thioglycolate (219.30 μL, 2 mmol) dropwise with ice cooling.7 The mixture was stirred at room temperature for 30 min and at 60° C. for 12 h, poured into water, and extracted with EtOAc. The extract was washed with water, dried, and concentrated, and the residue was suspended in EtOH and collected by filtration gave 8 as crystals; (271.34 mg, 60.5%). 1H-NMR (300 MHz, CDCl3): δ 8.00 (s, 1H), 7.83-7.78 (m, 1H), 7.55-7.51 (m, 1H), 7.26-7.19 (m, 1H), 4.46-4.39 (q, 2H), 1.46-1.41 (t, 3H). 13C NMR (300 MHz, CDCl3): δ 162.47, 159.25, 139.63, 137.60, 136.29, 129.75, 124.11, 116.24, 110.65, 61.74, 14.29.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f4725a47d6b4424ca74e2a89d784b891
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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